(2R,3S,4R)-2,4-Dimethyl-5-oxo-3-triethylsilanyloxy-hexanoic acid methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4R)-2,4-Dimethyl-5-oxo-3-triethylsilanyloxy-hexanoic acid methyl ester
• 英文别名: methyl (2R,3S,4R)-2,4-dimethyl-5-oxo-3-triethylsilyloxyhexanoate
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: GMZZHTUWKSDMJO-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2,4-Dimethyl-5-oxo-3-triethylsilanyloxy-hexanoic acid methyl ester 、 Carbamic acid (Z)-(1S,2S)-1-((S)-1-{(2R,3R)-3-[(2Z,7Z)-(4S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-9-oxo-nona-2,7-dienyl]-oxetan-2-yl}-ethyl)-2-methyl-hexa-3,5-dienyl ester 在 (+)-β-chlorodiisopinocampheylborane 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 17.5h， 生成 、 methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z)-11-[tert-butyl(dimethyl)silyl]oxy-15-[(2R,3R)-2-[(2S,3S,4S,5Z)-3-carbamoyloxy-4-methylocta-5,7-dien-2-yl]oxetan-3-yl]-7-hydroxy-2,4,10,12,14-pentamethyl-5-oxo-3-triethylsilyloxypentadeca-8,13-dienoate
  参考文献：
  名称：

  Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

  摘要：

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.172

文献信息

• Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites
  作者：Ian Paterson、Oscar Delgado

  DOI：10.1016/j.tetlet.2003.09.172

  日期：2003.12

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.